Top Retirement Don’ts

From the title you might expect this post to be full of “don’t do this” and “don’t do that” retirement advice.

But this “don’ts” post is a bit different.

It’s not focused on the things you should avoid to get to retirement.

Instead this post celebrates retirement greatness by listing the (annoying to terrible) things you don’t have to do once you retire.

It’s my top list of don’ts after 2.5 years of retirement.

I’m looking forward to the don’ts others have as well, so be ready to add yours in the comments below.

Even if you aren’t retired, go ahead and add your dream don’ts! This will be fun!

Before we get started I want to note that while it might sound like I hated my job/career, I actually didn’t. I would say I liked it (not loved it) and had many more highs than lows.

That said, I like doing whatever I want way better. 😉

With that out of the way, here are my top retirement don’ts in no particular order…

1. You don’t have to get up early unless you want to.

Haha! I started with a bang, right?!

I remember when I worked I had to drag myself out of bed every day. Especially on those cold, snowy, winter days.

Or when you knew the day was going to royally suck for one reason or another. It was brutal, but duty called and I had to get up.

Nowadays I actually get up earlier than when I worked, but it’s because I want to. The reason I want to is that I have an exciting day ahead of doing whatever I want to do versus what’s dictated by someone else.

If I’ve had a late night or just feel like I need some extra sleep, no worries. I just roll over and get up whenever the mood strikes me.

And it might go without saying, but there are certainly no alarm clocks involved in me getting up. I wake up when I wake up and get up when I decide to.

I’ve used an alarm clock maybe five times in the past couple years.

2. You don’t have to go to work (or anywhere) when you’re sick.

I had to re-live my previous nightmares in this area recently through my son.

He got a bad cold and had to go into work each day or suffer the consequences. (One of his jobs sent him home so others wouldn’t get sick but the other would have fired him if he hadn’t showed up.)

The situation made me recall the countless times I went into work and could barely keep my head up. But there was an important meeting/report/something else that had to be done that day and I was the only person on planet earth who could do it. So I went in.

Over my 28-year career I missed maybe 15 days because of illness. I worked many more days than that when I was sick.

Now if I get sick (which I haven’t been in some time), I get plenty of rest, drink lots of liquids, and recuperate at home as comfortable as I can make myself.

3. You don’t have to attend life-sucking meetings.

My last year of work I bet I broke the Guinness Book of World Records record for most yawns during meetings.

I would literally yawn multiple times during some meetings — so much so that I had to come up with a way of rubbing my mouth so it looked like I was opening it to rub my lips (which is about as bad as yawning).

But I yawned so much because I was BORED TO DEATH. The business was uninteresting and the fact that I reported to an uninspiring boss made it worse.

In fact, meetings without him were generally fine. But if he was in attendance, bring out the yawn-fest.

More on that in a moment…

Anyway, the last time I yawned since retiring was maybe after our horrendous 24+ hour trip to Grand Cayman. And even then it was a happy yawn followed by a great night’s sleep.

4. You don’t have to play politics.

If you work with people, you have to play politics at one time or another.

As you progress higher up within a company, it gets worse since you don’t only have to play for yourself, but for your employees, your division, etc.

It’s unfortunate, but is a fact of life.

And it’s mentally exhausting.

The only politics I play now is when I try to get my wife to spend more on a luxury vacation. She’s still holding on to her money-saving ways and needs a bit of coaxing sometimes. 😉

5. You don’t have to take orders from a bad boss.

During most of my career I had great bosses — people I respected and even admired. I was very fortunate.

But I had some bad ones as well.

I had 18 bosses in 28 years (and those are just direct bosses, not counting the people above them).

Of those there were a few nightmares — including the last one who pushed me into retirement.

I won’t go into detail about him but let’s say out of 18 he ranked #18. The worst.

And yet he was the boss. His word stood.

Of course by the time he was my boss I was financially independent and had been around the block a few times.

So I was much bolder at offering a counter-point when he suggested something crazy (which was often).

As you might imagine, he wasn’t too pleased with opposing opinions and we ultimately decided to part ways.

One of the best decisions of my life.

And now I don’t have to listen to a boss at all.

BTW, I’d love to hear your bad boss stories in the comments below. Maybe we can have a competition on who’s had the worst boss.

One story about my last boss for chuckles…

We were having a heated conversation, probably over something stupid, when he said, “Isn’t this business the most important thing in your life?” (not his exact words, I’m sure, but that was the meaning).

Without missing a beat I said, “No. No, it isn’t. It’s probably #5 or so at the highest.”

I thought his head was going to blow off his head! LOL!!!

6. You don’t have to handle employee and co-worker issues.

Of the 28 years I worked, I had co-workers for 28 years. Ha! Of course!

For 25 years I had employees who reported to me.

Just like with my bosses, most of these people (both co-workers and employees) were great. I enjoyed working with them. I also had a special fondness for my employees as their careers, work happiness, and satisfaction were placed in my hands. I wanted the best for them.

But just like any people (me included), many these folks had issues. And their issues became my issues.

A few examples of things I had to deal with:

  • Employees using the company credit card for non-work purposes and then not paying their bills each month as the card required.
  • Employees going through a high-drama divorce with each other.
  • Employees who failed drug tests and then claimed that someone had slipped them a bad brownie at a party.
  • Co-workers who ran into several cars in the parking lot and didn’t admit it until they were caught on tape.
  • Co-workers having affairs with their subordinates.

It went on and on. I’ve probably forgotten some of the worst stuff.

Then there were just the regular work-related issues of problems with projects, trouble with vendors, inter-departmental squabbles, etc. to navigate through.

It was often like I had children, all of whom were looking at me to solve their various issues.

I do not miss that in any way.

7. You don’t have to work during family time.

Have you ever worked late? I usually worked very late the first decade or so of my career.

Have you ever worked on weekends or holidays? I did all the time.

Have you ever worked on vacation? Ugh. Don’t ask.

I have example after example of working during time I was off and with my family. Most of the time the boss/company expected it and I had to go along.

No more.

8. You don’t have to manage vacation time when you have guests or want to travel.

Two weeks’ vacation. Wow, thanks for being so generous.

Even after I negotiated up to four weeks’ vacation (when switching jobs) and never let that go when moving to new jobs, it was still a balance to use the vacation time.

Not only did we have vacations we wanted to take but we also had visits to our home from family and friends. (Not so much in Michigan, but once we moved to Colorado, the floodgates opened!)

These days I don’t have to check and see how many vacation days I have left if I want to go somewhere or if someone decides to visit.

I’m free.

9. You don’t have to sit for eight hours a day.

This was a killer for me.

Day after day, year after year I was sitting for the vast majority each day.

Science has recently discovered how bad sitting is for a person.

Check this out:

Any extended sitting — such as at a desk, behind a wheel or in front of a screen — can be harmful. An analysis of 13 studies of sitting time and activity levels found that those who sat for more than eight hours a day with no physical activity had a risk of dying similar to the risks of dying posed by obesity and smoking.


Now I sit for a few hours a day but…

I also work out every day plus get in about 17,000 steps.

I’m hardly ever sitting for more than an hour without getting up and moving in one way or another. The fact that I drink so much water these days makes sure I’m up frequently. 😉

I certainly don’t miss the small aches and pains associated with being glued to your chair most of the day.

10. You don’t have to fight traffic.

Over my career I had good commutes (15 minutes or so) and bad commutes (an hour or more). In fact I had more of the former than the latter, so I got off pretty easy compared to most.

I had a friend who used to live in New Jersey and work in NYC. He had a two-hour commute ONE WAY. Do the math on how four hours commuting adds up over a year and it’s pretty depressing.

Whatever length of commute you have, it probably stinks.

Not only does it add AT LEAST 30 minutes round trip to your day, but it’s expensive and, of course, it’s more sitting.

When we were first married we lived in Pittsburgh. Do you know how hilly it is in Pittsburgh? Do you know how much snow they can get there at one time? Do you know how little they are prepared for it?

One day it had snowed something like 15 inches the night before and the roads were a total mess. When I finally got through to a company representative (you had to call on a landline in those days), he insisted (despite my “are you SURE?” questioning) that the company was open.

I got into my car and plowed/slid all the way downtown for two hours. BTW, it was still snowing at this time.

Immediately upon getting to work I was informed that the offices were closed due to weather. Yes, this really happened.

So now I drove back home, in worse weather, and took THREE HOURS to do so. By the time I got home in the early afternoon, my nerves were totally frazzled. I kissed the ground, thankful that I was alive, and “enjoyed” the couple hours of freedom I had remaining in the day.

Obviously that’s an extreme case, but even a decent snowfall can make a big problem.

At my last company, the owner (the bad boss I described above) was so greedy that he would almost never close the office. The entire city might be shut down, but not our office.

When I told him that making employees drive during terrible conditions was putting their safety at risk, he wondered if I “really cared” about the business. And this was from a company that touted their care for employees. They had even won several “best workplace” awards.

It was total hypocrisy.

Anyway, whether it’s a regular commute or a terrible one, I don’t play that game any longer.

11. You don’t have work-related stress (or much stress at all).

I’ve said previously that I didn’t really realize how much stress I had until I quit work. Then I could quite literally feel it draining out of my face (where most of the tension resided) and body over time.

It took six months or so to leave completely.

These days, there is no work stress, which was probably about 80% of my overall life stress. Of course there are still life things that pop up and cause stress but it’s nowhere near what I had when working.

I have also became very sensitive to stress. I can feel it coming on me now whereas for 28 years it was simply my constant companion. This is one reason we had to take 10-day vacations — because it took three days for me to de-stress enough to begin enjoying it.

12. You don’t get the Sunday afternoon pit-in-the-stomach feeling.

I was thinking about this last Sunday afternoon.

I was closing the curtains for the evening and thought, “Wow. If I was still working, I would have a huge sense of dread right now as I know I’d be facing a new week soon.”

Instead, I went downstairs and enjoyed a movie with my wife.

Does anyone get those pit-in-the-stomach, dread-fearing, sense of hopelessness feelings about 3 p.m. on Sunday?

Ok, so maybe it’s not that bad, but you know what I mean, right? You know the weekend is coming to an end (just after it got started!) and another week of hard work, long hours, bad bosses, and tough co-workers is ahead of you.

And you feel the dread associated with the impending doom.

No, thank you. That’s a sure “don’t” for me.

13. You don’t have to answer texts at 11 pm.

My last boss used to text me late at night to tell me super urgent and life-threatening things like we had a misspelling on a page of our massive website.

Of course I had to respond or else 1) see a flood of extra messages wondering why I wasn’t combing the website myself or 2) face the same grilling in-person the next day.


These days I usually go to bed around 10 p.m. (since I get up early), so even if someone does text me then, I’m asleep.

14. You don’t have restless sleep thinking about the next day.

I never knew how well I could sleep until I retired. It’s so peaceful now.

I was talking to my wife the other day about dreams and realized that I hadn’t had an anxiety dream in as long as I remember.

That was not the case when I was working. I had anxiety dreams fairly often and almost nightly I would wake up with some business matter on my mind.

Now if I wake up the only question on my mind is do I get up to use the bathroom or can I hold it until morning. 😉

15. You don’t have to go out when there are crowds.

I dislike crowds.

Not only are they a pain to deal with but they often turn a nice event into a hassle.

But when you’re retired, you can avoid crowds by going places when they are at work.

Here are a few examples of how this plays out for us currently:

  • At the gym I used to work out after work (6 p.m.) and it was packed. (Not to mention I was mentally exhausted from work.) I now work out at 7:30 a.m., just after the crowd leaves to go to work.
  • We used to shop at the grocery store on weekends. It was packed. Now we go during the weekday (and we usually walk there and back.) I hardly ever wait for anyone ahead of me in a checkout line.
  • Just thinking of going to a movie on a Friday or Saturday night gives me the willies. Even going at night during the week is bad enough. We now go in the late morning or early afternoon on Tuesdays. There’s almost no one there (many times we have the theater to ourselves), plus the tickets are discounted!

Name almost any place you might go — restaurant, coffee shop, doctor’s office, DMV, tourist location, etc. — and there’s a busy time and a not-so-busy time.

We go when others don’t, which makes the event pretty pleasurable.

16. You don’t have to skip events because you have to work the next day (or are too tired).

How many times was I invited to an event, party, etc. and I refused because I either had to work the next day or was too tired from work to go in the first place?

One example: Super Bowl parties.

I used to get invited but since we lived on the East Coast and the game would run late, I’d decline because of work.

We now get there early and are usually the last ones to leave.

Many working people don’t come or end up leaving in the third quarter because they “have work the next day.”

That’s fine with me — they leave lots of food behind and, as I said above, it’s generally better without a crowd! 🙂

17. You don’t have to shave every day.

I dislike shaving.

And though I’m no Grizzly Adams (it would take me a few years to grow a decent beard), I still had to shave every day while working. After all, I worked in a professional environment that required it.

Now it’s Mondays and Fridays — those are the days I shave.

So sweet.

18. You don’t have to wear uncomfortable clothes.

I started my career when wearing suits was the norm.

Things changed over the years, of course, and got more casual, but as I progressed up the ladder we never had as much clothing leeway as most employees did.

Plus, what we considered “comfortable” at work is nowhere close to retirement comfortable.

These days I wear athletic gear almost exclusively. It’s very comfortable. In the summer it’s shorts and a t-shirt. So, so comfortable.

If I have to even wear jeans or heaven forbid Dockers these days, I feel uncomfortable in them. They are tight, made from un-soft material, and feel very constricting.

I need my comfy clothes and that’s what I wear.

And no, I haven’t gotten to the point where I wear PJs out of the house, though I’m thinking they are probably acceptable attire for any Walmart trips I might make.

What’s the Point

So, what’s the point of all this “here’s how great retirement is” talk?

First of all, reading through this, I’m just so thankful. I wish I had retired much earlier. But am grateful that I finally came to my senses and retired when I did. If I hadn’t done that I could still be working and have over a decade more ahead of me.

Second, I realize how peaceful retirement is. I hope you have the same feeling when you retire.

Finally, it’s to show how great retirement is and encourage people to retire as soon as you can. Don’t make my mistake and wait a decade after reaching FI to retire. Do it as soon as possible and these can be your don’ts as well.

Now let me turn it over to you. Any retirees out there who have some don’ts I missed?

Or maybe you’re not yet retired but looking forward to some don’ts of your own. What are they?


Originally posted at

→ Save time. Save paperwork. Save dollars. Esurance ←